


Naughty and Nice

by JingleBee



Category: Free!
Genre: Anal Sex, Crossdressing, Degradation, M/M, Maids, Praise Kink, Smut, Spanking
Language: English
Status: Completed
Published: 2017-12-12
Updated: 2017-12-12
Packaged: 2019-02-13 21:07:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,097
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12992541
Author URL: https://archiveofourown.org/users/JingleBee/pseuds/JingleBee
Summary: One maid. Two masters. Each has a different way of taking care of their servant...





	Naughty and Nice

**Author's Note:**

> its ya boy

It was seven thirty in the morning on the estate owned by Rin Matsuoka and Sousuke Yamazaki. Aiichiro was in the bathroom connected to his special chambers, putting the finishing touches on his maid uniform. The uniform was black with white trim, came with a white apron, headband, and a bright red bow on the neck. On the surface he looked like an innocent, normal maid ready to start the day. However beneath the surface Aiichiro wore black lingerie. Black, lacy garters that held up his fishnet stockings, and matching thong panties that uncomfortably rode up into his bottom. Aiichiro looked at himself in the mirror and sighed as he gave a little twirl. As much as he didn't enjoy wearing the undergarments, he had to admit, the rest of the outfit looked good on him. It matched well with his pale skin, and hugged his girlish frame just right. He could almost call himself adorable. Aiichiro smiled at his reflection as he left to begin his duties.

* * *

 

First order of business, tend to Rin Matsuoka, the co-owner of the estate. Rin and his business partner Sousuke had been best friends since childhood, almost inseparable. It made sense that the two would share the estate with each other. Aiichiro's orders were to bring Rin his coffee. Rin was awfully cranky first thing in the morning, and without the stimulation of caffeine to ease his busy nerves, would only get worse throughout the day. Aiichiro carried the tea set on its tray into Rin's large office, decorated with paintings of his family. There, Rin was sitting at his desk, on call with another associate of his business. Aiichiro strode towards him with a cheerful smile.

"Good morning, Master Rin!" Aiichiro beamed.

"Yeah, yeah." Rin waved him off.

Aiichiro got right to work, setting a small coffee cup on Rin's desk and pouring as he talked on the phone about things a little maid like Aiichiro wouldn't understand. Then suddenly, Aiichiro's little button nose started to itch inside. Before he had time to think, he sneezed.

"Hey!" Rin yelped.

As Aiichiro sniffled, he realized what he'd done. As he sneezed, he accidentaly knocked over Rin's coffee. Right onto his lap.

"Ahh! I'm so sorry!!" Aiichiro apologetically squealed.

"Don't be sorry, clean this up!" Rin ordered.

Aiichiro searched around for something to dab Rin's lap with. A towel. A napkin. But he found nothing.

"Um...I don't have a napkin or anything..."

Rin then get a devious idea. He hung up his phone and stared at Aiichiro with an mischievous look.

"Use your mouth."

"H-huh!?" Aiichiro's eyes widened at the suggestion.

"You heard me! Take responsibility for your mess!"

Aiichiro gulped. He had no other choice.

"Y-yes, master."

Defeated, he dropped to his knees in front of Rin, and placed his small mouth on Rin's crotch. He began to suck the bitter liquid from his master's expensive pants. He sucked and licked as best he could, his face turning a deep red at the intimacy of his actions. Rin's soft sighs spurred him on to suck even harder, especially on Rin's growing manhood. After a while, Aiichiro noticed there was no more left. Although there was still a stain. Aiichiro stood to his feet and bowed.

"I'm sorry, master Rin! I tried my best to get it all out."

"Good. Because now you have to take care of this." RIn said, grabbing Aiichiro's hand and placing on his damp crotch, giving the maid a good feel of his erection.

"I...I don't understand..."

"I think you understand just fine." Rin said.

With one swift motion, the poor maid was bent over his master's desk, with one of his hands behind his back, giving Rin a good view of what was underneath his skirt. Rin hiked it up even further, revealing his plump bottom under his garter and panties.

"Don't look!" Aiichiro begged.

Rin ignored, tugging on Aiichiro's panties and revealing more of his bottom. He started to give a low cackle.

"Nice undies." Rin mocked.

Aiichiro gulped and closed his eyes, just waiting for whatever Rin had in mind to happen. He opened them again when he felt a sharp slap on his behind.

"Ow!"

The room started to fill with the sound of claps as Rin began his relentless assault on Ai's ass. As his cheeks began to burn, the pain started to turn into some twisted form of pleasure. Ai could feel himself hardening in his panties with each spank. His cries of pain softened into whimpers of need. His body started to react on his own, wiggling his hips to silently beg for more.

"Starting to enjoy this, huh?" Rin asked. But it sounded more like teasing.

The smacks ended, and Aiichiro started to meekly stand, but Rin shoved his face into his desk once more.

"Where do you think you're going, little slut?"

"S...sorry...master."

Aiichiro laid limp on the desk, easing himself for whatever came next. The sudden intrusion of Rin's hot hardness into his small hole brought him back to reality. Rin was quite large, stretching the maid to his limits. Ai groaned and balled his fists. The lack of proper lubricant did a number on Ai's entrance. Once Rin was properly buried in his little maid, he started to pull out, only to roughly plunge back inside. In and out, harder and harder, Ai was forced into the desk by Rin's thrusts. When Rin found that special spot inside of him, Ai moaned like a bitch in heat.

"Please...stop...." Ai begged, managing to pull himself together.

"What do you mean stop? We only just started your punishment. Besides, I know a slutty maid like you is probably enjoying this." Rin said, dotting his sentences with animalistic grunts.

"I...I'm not."

Rin gave another row of smacks to Ai's blushing bottom.

"Don't lie to me!"

"Ah! Sorry..."

"Good. Now tell me how much of a slut you are!" Rin commanded as he got more violent with his thrusts.

"I...I'm your bitch. Please punish me! Punish this slutty maid even more!"

"That's a good little whore." Rin said smacking him once more.

Rin fucked into the boy even harder and faster, hitting that sweet spot over and over, driving Ai to the edge.

"Master..." Ai panted.

"What is it?"

"I want to come....please let me come."

"Heh. Now you show your true colors. Fine. I guess I'll allow it this time." Rin said.

"Thank you master!"

With a few more thursts, Rin unloaded inside of his slutty little maid with a growl, and Ai followed with a girlish yell, releasing himself all over the underside of Rin's desk. Beofre he had time to catch his breath, Rin grabbed a fistful of Ai's silver locks.

"I hope you learned you lesson today."

Ai meekly nodded in Rin's grasp.

"Good. Now get out of here." Rin said, tossing him aside.

"Yes, master Rin."

* * *

 

Next up on Aiichiro's duties, checking up on Sousuke and seeing if he needed anything. Sousuke could usually be found in the estate's gym, doing physical therapy for his shoulder, which was injured during childhood. Poor Sousuke, Aiichiro thought. He always worked so hard. IIn the gym, there was Sousuke, doing some work on his arm.

"Good evening, Master Sousuke!" Ai beamed.

Sousuke merely looked at him with his cold, blue eyes. He was always so intimidating.

"C-can I get you anything, master?" Ai asked.

"No. I'm fine." Sousuke said.

Ai bowed. He noticed that his regular clothes were laid in a pile to the side. He decided to take it upon himself to gather them and take them to the laundry room. He bent down to pick them up, and Sousuke spoke.

"Aiichiro...what's that?"

"Hmm? What's what?"

Sousuke released his grip on the machine and strode towards him, lifting up his skirt.

"Ah!"

"This. Your ass is all red."

Aiichiro remembered his earlier encounter with Rin. In fact, he hadn't forgotten.

"Oh! Th-that's nothing, I swear!" Aiichiro tried to ease Sousuke's worries.

"Hmph." Sousuke grunted.

Suddenly, he grabbed Aiichiro's wrist tight, and dragged him along.

"Come on."

"Where are we going?"

"Just come."

Aiichiro was led out of the gym, into the long halls of the estate. Turn after turn, passing room after room until they finally arrived in their destination. The infirmary for the houses workers.

"What are we doing here?"Aiichiro said, looking around at the white room.

"Get on the bed." Sousuke commanded.

Aiichiro whimpered at Sousuke's commanding tone, and did what he said twice as fast as normal. He watched as Sousuke dug around in cabinets, finally pulling out a small pink bottle. Sousuke walked over and ordered him once more.

"Get on your hands and knees."

"Yes sir."

Ai did what he was told and Sousuke got on the bed behind him. He felt a chill as he poured whatever was in the bottle on his sore bottom.

"What's that?"

"Chamomile lotion."

Sousuke spread the viscous gel on his bottom. Aiichiro sighed. He couldn't help but feel it's soothing effects, especially after all that pain.

"That feel good?"

"Y-yes master."

Aiichiro laid his head on the pillows, letting his master take care of him. Then suddenly, Sousuke pulled his panties aside, to poke and prod at his entrance with his lotion covered fingers.

"M-master? What are you doing?"

"I need to get deeper. Looks like you've been hurt inside too."

Ai gulped in embarrassment. But soon his embarrassment was replaced with pleasure as Sousuke's thick, smooth fingers worked his insides.

"Master..." Ai sighed.

Soon, much to Ai's dismay, Sousuke slipped his fingers out of him. He looked back only to see Sousuke lining himself up to put his cock inside.

"What are you..."

"I told you, I need to get deeper."

Sousuke's manhood filled him just like Rin's, only without much resistance because his insides were coated with lotion. Ai gave a soft, deep moan, and grabbed at the pillows.

"How do you feel, Ai?"

"I...it feels good, master."

"Good boy. You're being so brave right. now."

"Thank you, master!"

Sousuke lifted Ai's leg, turning him over from his position on his hands and knees, and moving him so that they were facing each other.

"God you feel so good, Ai." Sousuke praised as he softly thrust into the boy.

Ai gyrated his hips in time to meet his master's, practically fucking himself on Sousuke's cock. He started to whimper and moan even more. Sousuke leaned down to get closer to Ai's face. Their blue eyes met, and Sousuke captured his lips with a kiss.

Ai wrapped his arms and legs around Sousuke, pulling him in to deepen their kiss. Soon they parted so Sousuke could praise him little maid once more.

"You're being so good, Ai. Such a good little maid. So pretty for me." Sosuke said dotting his sentence with soft thrusts.

"Master...more...please." Ai begged for faster movements.

"Anything for you, my sweet boy." Sousuke smiled down on him.

Sousuke picked the boy up, until he was sitting on his lap. The better to carry the boy, and maneuver him up and down on his length, like he was basically a cock sleeve. Ai held onto Sousuke for dear life.

"You want to come, baby?" Sousuke asked.

"Yes! Please master!"

"Good boy."

Sousuke picked up the pace, fucking into the little maid even more, and hitting that special spot inside of him more and more. With one hand he held onto Ai, and with the other, started to stroke Ai's own hardness from inside his panties. Ai moaned even more, fucking himself on Sousuke's cock and hand until he released with a yell.

"Good boy. Let it all out." Sousuke grunted, milking Ai and himself until he followed in AI's footsteps, releasing his seed inside of the boy with a loud grunt.

Ai collapsed in Sousukes arms, panting as the last of his cum leaked out.

"Was that good, sweetie?" Sousuke asked.

"Yes. Thank you master."

* * *

 

Aiichiro's duties were done for the day. It was late, and Rin and Sousuke were turning in for the night, as was he. As he undressed from his uniform, stockings and garters, he decided to leave on his lacy undergarments. He had started to grow accustomed to them, just like he grew accustomed to working here. Not only was the pay good, but there were other benefits of working with Rin and Sousuke as well. He slipped into bed, to rest himself. In the morning, it would be more of the same.

 

**Author's Note:**

> you already know who it is


End file.
